1. Obito- No. Just no.
2. Deva Path- Nope. He died to him, remember?
3. Danzo- He'll just spam Izanagi
4. Gaara- He might have a chance here actually.
5. Mei- I suppose. If he can get past her Acid mist.
6. Sasuke- I highly doubt it if he's EMS.
7. Neji- Probably.
8. Sakura- No doubt :|
9. Kiba- Yeah
10. Tsunade- Probably. Unless Kamui doesn't connect.
11. Hiruzen- Im Skeptical about this one.. It could be a draw with RDS But that would take some preparation time. And Kakashi could use Kamui in that time frame.
12.Base Naruto(NO SM, or KCM,or BM)- When naruto mastered Rasen-Shuriken Kakashi stated he surpassed him.
13. Weakened Itachi- Itachi has always been weakened by illness. I highly doubt Kakashi could beat him.
14. Shikamaru- Maybe
15. Darui- They're in the same league. Honestly this could go either way.
16. Jugo- Maybe.
17. Kimimaro- Maybe
18. Temari- Lightning is inferior to wind but Kakshi is known as the copy ninja, who has copied/learned over 1000 techniques.
19. Genma- Probably
20. Iruka -Yes.
You may think too highly of Kakashi.. He is about Low Kage rank but still. You named waaaaay too many people. Just my opinion.